Hydrazine hydrate (1:1) → HCID 178515509, compound

HRID 220160Notes

Reaction equation

HRID 220160 reaction equation
O.[NH2:2][NH2:3].[O:4]1[C:8]2([CH2:13][CH2:12][CH:11]([C:14]3[N:19]=[CH:18][C:17]([C:20](=O)[CH2:21][C:22]([O:24]C(C)(C)C)=O)=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[O:7][CH2:6][CH2:5]1>O1CCOCC1>[O:4]1[C:8]2([CH2:13][CH2:12][CH:11]([C:14]3[N:19]=[CH:18][C:17]([C:20]4[CH:21]=[C:22]([OH:24])[NH:3][N:2]=4)=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[O:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69055727Tert-butyl 3-(6-(1,4-dioxaspiro[4,5]decan-8-yl)pyridin-3-yl)-3-oxopropanoate

Product 1

HCID 178515509HCID 178515509, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Hydrazine hydrate (5 mL) was added to a solution of Example 93C (1.07 g, 2.96 mmol) in dioxane (10 mL). The resulting solution was refluxed for 3 hours before it was cooled and partitioned with tetrahydrofuran and brine. The aqueous phase was acidified with 6 N hydrochloric acid to pH 2 and extracted repeatedly with a tetrahydrofuran/ethyl acetate mixture. The combined organic phases were dried (magnesium sulfate), filtered, and concentrated. The crude product was recrystallized from ethyl acetate and hexane to provide a light brown solid.

Workup

  1. temperatureThe resulting solution was refluxed for 3 hours before it
  2. temperaturewas cooled
  3. custompartitioned with tetrahydrofuran and brine
  4. extractionextracted repeatedly with a tetrahydrofuran/ethyl acetate mixture
  5. dry with materialThe combined organic phases were dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was recrystallized from ethyl acetate and hexane
  9. customto provide a light brown solid

Sources & evidence

ORD record
ord-e76d8ec905aa44c4bac4324cbba4bf4e
Source dataset
uspto-grants-2012_06
Patent number
US08202878B2

Reaction notes

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